Iodoethane → HCID 58572422, compound

HRID 1927302Notes

Reaction equation

HRID 1927302 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH3:19].C(OCC)(=O)C.CCCCCC>CN(C)C=O.O>[Br:1][C:2]1[C:7]([O:8][CH2:18][CH3:19])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 232169621-(2-Bromo-3-hydroxyphenyl)ethanone

Product 1

HCID 58572422HCID 58572422, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, 1-(2-bromo-3-hydroxy phenyl)ethanone (6.50 g, 30.2 mmol), which had been obtained in Reference example 1(1c), and potassium carbonate (8.36 g, 60.5 mmol) were dissolved in N,N-dimethyl formamide (60 mL), and stirred at room temperature for 10 minutes. Subsequently, ethyl iodide (3.14 mL, 39.3 mmol) was added to the mixture, which was then further stirred for 21 hours. Ethyl acetate/hexane (1:1, V/V) and water were added to the reaction solution for fractionation, and the aqueous layer was extracted with ethyl acetate/hexane (1:1, V/V). The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate, 100:0-85:15, V/V) to give the title compound as a colorless oily substance (4.89 g, yield 67%).

Workup

  1. stirringwas then further stirred for 21 hours
  2. extractionthe aqueous layer was extracted with ethyl acetate/hexane (1:1, V/V)
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate, 100:0-85:15, V/V)

Sources & evidence

ORD record
ord-7c814cb6904746ac8b9514feceabf19c
Source dataset
uspto-grants-2012_05
Patent number
US08183272B2

Reaction notes

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